Windward Coast Vacation Rentals

Compare Vacation Rentals & Rent By Owner Homes in Windward Coast, USA

PRIVATE BEACHFRONT RENTAL
FromAU $741 per night
10.0 (176 Reviews)
1 Bedroom 2 Guests
Sunny Kailua Home w/Covered Lanai 1 Mi to Beach!
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10.0 (1 Review)
3 Bedrooms 7 Guests
Luxurious five-bedroom modern retreat
10.0 (1 Review)
5 Bedrooms 18 Guests
Modern Luxury Beach House Kailua
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9.2 (87 Reviews)
3 Bedrooms 9 Guests
Hawaii's Hidden Hideaway Bed & Breakfast
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8.4 (67 Reviews)
1 Bedroom 2 Guests
'Kailua Lani Suite' short walk to Kailua Beach. Air conditioned and private.
10.0 (120 Reviews)
1 Bedroom 2 Guests
Beautiful Guest House Kailua Beach
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9.1 (70 Reviews)
1 Bedroom 2 Guests
Available and legal for stays less than 30 days.
10.0 (114 Reviews)
1 Bedroom 2 Guests
Cozy Custom Vacation Home
FromAU $628 per night
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9.0 (10 Reviews)
3 Bedrooms 8 Guests
Charming Lanikai Kailua Cottage! Close to Lanikai beach, A/C, parking.
10.0 (108 Reviews)
1 Bedroom 2 Guests
Beachfront spectacular Kailua beach
FromAU $1,749 per night
9.0 (1 Review)
4 Bedrooms 8 Guests
Kailani Loft, Kailua Coconut Grove 1-bedroom
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8.6 (52 Reviews)
1 Bedroom 3 Guests
KAILUA-STEPS TO THE BEACH
FromAU $264 per night
10.0 (88 Reviews)
2 Bedrooms 5 Guests
Waimanalo Beach Cottages
8.4 (30 Reviews)
39 Bedrooms 50 Guests
BEACHFRONT! Barefoot living on the best spot on Lanikai Beach!
10.0 (77 Reviews)
1 Bedroom 4 Guests
Paradise Bay Resort
FromAU $605 per night
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8.0 (458 Reviews)
29 Bedrooms 23 Guests
Private One Bedroom Side House close to Kailua
3.5 (2 Reviews)
1 Bedroom 2 Guests
Footsteps to Hawaii's Best Beach
FromAU $218 per night
10.0 (55 Reviews)
1 Bedroom 2 Guests
Charming Apartment in Prime Location – Steps from Kailua Beach & Town
10.0 (35 Reviews)
1 Bedroom 3 Guests
Lanikai Ohana Hale
FromAU $1,395 per night
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New
1 Bedroom 4 Guests
Upscale Kailua Getaway: Steps to Swim Beach!
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New
3 Bedrooms 6 Guests
A Place of Peace - where heaven meets the Ocean
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New
2 Bedrooms 4 Guests
The Banyan Beach Bungalow
FromAU $507 per night
10.0 (26 Reviews)
1 Bedroom 2 Guests
@ Marbella Lane - Sunshine Seascape Ocean View
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New
4 Bedrooms 8 Guests
Lovely Private Kailua Cottage
FromAU $674 per night
10.0 (22 Reviews)
1 Bedroom 4 Guests
Beautiful Beachside Bungalow
FromAU $517 per night
10.0 (15 Reviews)
1 Bedroom 2 Guests
Kalama Room
FromAU $149 per night
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New
1 Bedroom 2 Guests
La Bella’s Bed & Breakfast-Honu (Turtle) Suite-Walk to beach-In Kailua (O’ahu)
10.0 (14 Reviews)
1 Bedroom 4 Guests
Newly Upgraded Private Home in Kailua
New
1 Bedroom 4 Guests
Kailua Beach/Lanikai LUX apartment w/Ocean Views from Rooftop Sun Deck
10.0 (12 Reviews)
2 Bedrooms 2 Guests
Beach Studio with private yard in Lanikai - 30 day Minimum Stay
10.0 (9 Reviews)
1 Bedroom 2 Guests
A Place of Peace - where heaven meets the Ocean
10.0 (5 Reviews)
2 Bedrooms 4 Guests
Coconut Grove Cottage, Walk to Beach and Downtown
10.0 (4 Reviews)
2 Bedrooms 4 Guests
Kailua Condo/Townhouse on Oahu 30 day period 7 day min
10.0 (3 Reviews)
2 Bedrooms 5 Guests
Affordable Island Getaway with private yard
10.0 (2 Reviews)
1 Bedroom 2 Guests
Charming 1.5 bedroom cottage, fully furnished in a great location!
10.0 (1 Review)
1 Bedroom 2 Guests
World Famous Kailua Beach Charming Cottage
10.0 (1 Review)
1 Bedroom 2 Guests
The Perfect Escape
FromAU $181 per night
10.0 (1 Review)
1 Bedroom 4 Guests
Gorgeous 2 bedroom bayside house on Windward side of Oahu
9.8 (72 Reviews)
2 Bedrooms 6 Guests
Beautiful Kailua Hale 1 Bedroom
FromAU $427 per night
9.8 (29 Reviews)
1 Bedroom 4 Guests
Cozy Kaaawa Studio with Mountain Views - 30 Day Min
9.8 (25 Reviews)
1 Bedroom 2 Guests
La Bella's Bed and Breakfast-Nai’a Suite-Walk to beach-In Kailua (O’ahu)
9.8 (12 Reviews)
1 Bedroom 3 Guests
Kaneohe Bay B&B Waterfront & mountain views galore~saltwater pool
9.6 (144 Reviews)
2 Bedrooms 4 Guests
Heavenly Hale Best monthly Vacation rental - walk to beach!
9.6 (4 Reviews)
2 Bedrooms 4 Guests
Absolutely Oceanfront - 60' Waterfall Lap Pool
9.4 (170 Reviews)
1 Bedroom 2 Guests
Kailua Oceanfront-60' Lap Pool - Upscale Quiet Neighborhood - Legal
9.4 (165 Reviews)
1 Bedroom 2 Guests
Ocean View Guest Cottage - 1990/NUC-1797
9.4 (102 Reviews)
2 Bedrooms 4 Guests

About Windward Coast Vacation Rentals

With more than 577 Windward Coast vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Windward Coast.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Windward Coast, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Windward Coast. Places to stay near Windward Coast are 1319.49 ft² on average, with prices averaging AU $1,121 a night.

RentByOwner makes it easy and safe to find and compare vacation rentals in Windward Coast with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Frequently Asked Questions About Windward Coast?

What are the top vacation rentals in Windward Coast?

How many Rentbyowner vacation rentals are available in Windward Coast?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 577 in the Windward Coast area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Windward Coast. 

Nearby Neighborhood (10)

NeighborhoodProperty Count
Eastern Honolulu Vacation Rentals in Windward Coast, US 148
Kalama Tract Vacation Rentals in Windward Coast, US 101
Lanikai Vacation Rentals in Windward Coast, US 63
Hawaii Kai Vacation Rentals in Windward Coast, US 57
Coconut Grove Vacation Rentals in Windward Coast, US 494
Enchanted Lake Vacation Rentals in Windward Coast, US 442
Keolu Hills Vacation Rentals in Windward Coast, US 423
Kuulei Tract Vacation Rentals in Windward Coast, US 483
Kamehame Ridge Vacation Rentals in Windward Coast, US 162
Queens Gate Vacation Rentals in Windward Coast, US 108